Dating again isn’t like riding a bike. When you get back on a bike, the shape and feel of it haven’t changed. But for many re-entering the dating world after long relationships, everything feels different. With most people now meeting online, the spontaneity of meeting someone at an event seems almost extinct. Men and women report being less likely to approach someone in real life when they can avoid the risk of rejection with dating apps that confirm mutual interest. While this can be convenient, it also introduces a whole new set of rules that can feel overwhelming. The fear of failure, rejection, and the unknown can make stepping back into dating seem paralyzing. Perhaps the key is to think of dating not as riding a bike again—but as riding one for the first time.
When my eldest daughter learned to ride a bike, she was thrilled. She jumped on, and within minutes, training wheels securely in place, she took off confidently. My youngest, however, was less confident. She didn’t want me to let go, fearing every little wobble would lead to a face full of pavement.
One afternoon, as we practiced on a rocky trail lined with pachysandra hills, I had an idea. Her fear of falling was so strong that she couldn’t move forward. So, I suggested we practice falling first instead of riding. She agreed. For the next ten minutes, she leaned off the bike and let herself tumble gently into the pachysandra. Then she pedaled a few turns and fell again. Soon, it became amusing. She realized she could survive the fall. And just like that, when we got back to riding, my hand left her back, and she was off on her adventure.
So, how do we embrace this next chapter as new cyclists in the dating world? First, let’s not let the unfamiliar bike scare us away. You’ll hear horror stories about online dating. There will be times when your dating pool feels like a barren wasteland. But I assure you, whether online or in person, there are wonderful opportunities to connect.
To start, let’s put on some training wheels with two mindset shifts:
Face the Worst-Case Scenario
Like my daughter, many of us are told to stop worrying and just be hopeful. But sometimes, the best way to move forward is to look our fears straight in the eyes. This is why monks practice Maranasati meditation—mindfully contemplating mortality. While it may sound dark, it actually helps people embrace life more fully by confronting their deepest fears.
So, what’s your worst-case scenario in dating? Will you struggle to find someone who shares your values? Will you have to build a fulfilling life surrounded by friends, family, and community instead? Will you, dare I say it, die alone? As difficult as these thoughts may be, confronting them can bring clarity. Fears left unchecked can lead to poor decisions—like settling for the wrong person just to avoid loneliness. Acknowledging our fears can shift us from stuck to taking action.
Create a Vision for a Great Life
A client of mine, Paul, felt stuck in dating frustration. Every swipe seemed to end in a canceled date. He was kind, handsome, intelligent, and successful—by all accounts, he shouldn’t have been struggling. But each disappointment chipped away at his confidence, leaving him anxious that his best years were slipping away. He began wondering if something was fundamentally wrong with him. It was disheartening, and soon, he started retreating from dating altogether.
To quote The Shawshank Redemption, Paul needed to “get busy living or get busy dying.” So, we shifted focus from dating to living. We outlined what a great life looked like for him, based on his core values. He realized that in his search for a partner, he had neglected things that once brought him joy. He had been community-minded, but his divorce and dating struggles had pulled him away from service. He used to be an avid cyclist, but co-parenting and work had pushed that aside. And he valued deep friendships, yet he hadn’t been as open with others as he was with his closest friend.
Together, we built a roadmap—not for dating, but for thriving. Paul started volunteering at a homeless shelter with like-minded people. He found a cycling group that fit his schedule. He practiced being more open and vulnerable in new friendships. Four months later, Paul checked in. While he still wanted a partner, his dating anxiety had transformed. He was no longer seeking validation from women—he was focused on whether they shared his values and could celebrate his best life with him.
I’d love to tell you he found “the one” right away, that he met a wonderful woman on a group ride, and they lived happily ever after. But the story is still being written, just like yours. And maybe that’s the point. Life is an adventure, and if we chart our course with intention, the journey can be breathtaking, fulfilling, and full of joy—regardless of the outcome.
Ready to create your map? Schedule a coaching sessions where we’ll identify your values, chart a roadmap for a great life, and explore online and in-person dating strategies that align with what truly matters to you. Let’s create a next chapter worth loving.
留言